The Ups and Downs of Being Round is a coming of age story about a girl who struggles throughout her life with issues of weight. Overweight as a child, Madison Jenson struggles with teasing and physical limitations until she loses the weight during her adolescent years. Just as she begins to enjoy life as a slim girl she gains the weight back during her college years. Finally, being fed up with being unhappily overweight, she loses it again as a young adult, but to her surprise she loses a lot more than just the weight and finds out that physical weight loss does not guarantee happiness.